Sodium Iodide → HCID 137010693, compound

HRID 2206233Notes

Reaction equation

HRID 2206233 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18]C)[C:12]=2[C:11]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]3[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)=[N:10]1.[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[C:32]([N:29]1[CH2:28][CH2:27][CH:26]([C:23]2[CH:24]=[CH:25][C:20]([C:11]3[C:12]4[C:13](=[O:18])[NH:14][CH:15]=[CH:16][C:17]=4[N:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[N:10]=3)=[CH:21][CH:22]=2)[CH2:31][CH2:30]1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 117988165HCID 117988165, compound

Product 1

HCID 137010693HCID 137010693, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(4-(4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)piperidin-1-yl)ethanone (112 mg) in acetonitrile (3 mL) were added sodium iodide (73 mg) and chloro(trimethyl)silane (0.155 mL), and the mixture was stirred at 60° C. for 3 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel, hexane/ethyl acetate to ethyl acetate/methanol). The obtained fraction was purified by HPLC (L-Column 2 ODS, mobile phase: water/acetonitrile (containing 10 mM ammonium carbonate)) to give the title compound (51 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (silica gel, hexane/ethyl acetate to ethyl acetate/methanol)
  6. customThe obtained fraction was purified by HPLC (L-Column 2 ODS, mobile phase: water/acetonitrile (containing 10 mM ammonium carbonate))

Sources & evidence

ORD record
ord-857cf59909024069bd6aa9d758f0ca6b
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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